Total synthesis of (+/-)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group.
Ergot alkaloids and their synthetic analogs have been reported to exhibit broad biological activity. We investigated direct construction of the C/D ring system of ergot alkaloids based on palladium-catalyzed domino cyclization of amino allenes. With this biscyclization as the key step, total synthesis of (+/-)-lysergic acid, (+/-)-lysergol, and (+/-)-isolysergol was achieved.
Inuki
Shinsuke
S
Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto, Japan.
Oishi
Shinya
S
Fujii
Nobutaka
N
Ohno
Hiroaki
H
D000466:Alkadienes / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004873:Ergolines / Q000138:chemical synthesis*; D007211:Indoles / Q000737:chemistry*; D008237:Lysergic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000466:Alkadienes; D004873:Ergolines; D007211:Indoles; C025947:propadiene; D010165:Palladium; D008237:Lysergic Acid; C061884:lysergol; D001966:Bromine